Itinerary
NOTE: The schedule below is subject to change.
SUNDAY, JULY 8
CHESTERTOWN, DOUGLASS SITES, EASTON
This journey into the complexities of American history begins, fittingly enough, in Chestertown’s historic Custom House, home of the C.V. Starr Center for the Study of the American Experience. A 1746 landmark on the Chester River, the Custom House itself, as we will discover, embodies many of the paradoxes of freedom and slavery in America. From Chestertown, the group will travel south to Caroline County, birthplace of Frederick Douglass, whose powerful oratory, brilliant writing, and political activism profoundly redefined the concepts of freedom and citizenship. From Douglass’s birthplace along the Tuckahoe River, we will follow in his footsteps to the extraordinarily preserved Wye House, the Talbot County plantation where he resided as a child, which is still owned by the 11th generation of the family that settled it in the 1660s. Wye, with its unbroken history stretching from the 17th century to the present, is an ideal place to connect with the past, and begin thinking about the themes of our weeklong journey. Renowned historian Ira Berlin will close the day in Easton with an address on the subject of his life’s work.
Daily bloggers: Jasper Colt, Jill Ogline
9:00 Sign in and introductions at the Custom House
11:00 Depart from Custom House
12:00 Frederick Douglass birthplace

Frederick Douglass, c. 1866
12:30 Arrive at Wye House, box lunch
1:30 Discussion and tour of grounds
3:00 Group discussion
3:45 Tour of Wye House with Mrs. Mary Tilghman
4:15 Musical performance by Sombarkin’ (Karen Somerville, Lester Barrett, and Jerome McKinney)
4:30 Depart Wye House
5:00 Arrive in Easton and meet with Councilwoman Moonyene Jackson-Amis, Talbot County Courthouse lawn
5:30 Check in Tidewater Inn
6:00 Dinner at Tidewater Inn
7:00 Lecture and discussion with Ira Berlin, Distinguished University Professor, University of Maryland; author of several books on slavery, including Many Thousands Gone: The First Two Centuries of Slavery in Mainland North America and Generations of Captivity: A History of Slaves in the United States.
8:30 Free time
MONDAY, JULY 9
OLD POINT COMFORT, COLONIAL WILLIAMSBURG
Moving down the Delmarva Peninsula and across the mouth of the Chesapeake Bay to the peninsulas forming the heart of early colonial society, the second day of our journey will explore the beginnings of slavery in the colonies. After a morning on the road, we will visit Old Point Comfort, the little-known site where Virginia’s first enslaved Africans landed in 1619 – and which also played an equally key (and equally unknown) role in the liberation of African-Americans two and a half centuries later. We will also begin to talk today about the reasons that slavery remains a difficult topic for many people to confront, and the ways in which teachers might approach the subject with their students. The end of the day will bring us to Williamsburg, a site rich in history and in contradictions – both historic and contemporary.
Daily bloggers: Karen Frison, Carrie Happoldt
7:30 Breakfast at Tidewater Inn
8:30 Depart Easton
12:00 Lunch in Hampton, VA
The Emancipation Oak, Hampton, VA
1:00 Tour of Old Point Comfort led by Adam Goodheart, Director of the C.V. Starr Center for the Study of the American Experience
2:30 Depart Old Point Comfort
4:30 Arrive in Williamsburg
5:00 Check in at Woodlands Hotel
5:30 Dinner at King’s Arms Tavern
6:30 Lesson plan workshop at Woodlands Hotel led by Darryl Calloway
8:00 Free time
TUESDAY, JULY 10
WILLIAMSBURG
Once in Williamsburg, the group will tighten its focus on the intertwined roots of slaveholding and independence, as well as the states of partial freedom that characterized the lives of many colonial Americans in the 18th century, black and white alike. Living history programs by interpreters portraying free blacks, middling landowners, enslaved artisans, prosperous planters, and rural slaves will personalize the complexities of a society deeply stratified by race, class, and gender, yet enthusiastically embracing expanding definitions of democracy. We will also talk with some of Colonial Williamsburg’s master educators about how they face the challenges of presenting slavery honestly, yet sensitively, to millions of diverse visitors each year.
Daily bloggers: Kathryn Riley, Anna Green
7:30 Breakfast at Woodlands Hotel
8:30 African Americans in 18th-Century Virginia (Woodlands Hotel)

Colonial Williamsburg interpreters
portray a scene from domestic slave life
9:30 Case Study: Matthew Ashby
12:00 Lunch at Chowning’s Tavern
1:00 African-Americans in the Trades
1:45 Meet a Founding Father (Thomas Jefferson or George Washington)
3:00 Daily Life: Urban Slavery (Peyton Randolph House)
4:00 Daily Life: Rural Slavery (Great Hopes Plantation)
5:00 Panel discussion with Rex Ellis, Williamsburg VP of the Historic Area
6:00 Dinner at Christiana Campbell’s Tavern
7:00 Free time
WEDNESDAY, JULY 11
WILLIAMSBURG TO ST. MARY’S CITY
Sailing up the Chesapeake Bay from Yorktown to St. Mary’s City aboard the aptly named North Star, we will discuss the routes over both water and land that slaves followed when escaping from bondage. Joining us on the daylong voyage is historian T. Stephen Whitman, who – as we cross over from Virginia into Maryland – will talk about resistance to slavery, including abolitionism and the Underground Railroad, within our own home state. We will hear the dramatic story of the schooner Pearl, a vessel that carried escaping slaves over these very waters in 1848. Approaching St. Mary’s City from the Bay just as the first settlers of Maryland did in 1634, we will land at the site of Lord Baltimore’s settlement and – appropriately enough – partake of a hardshell crab feast at the end of the day.
Daily bloggers: Erick Brown, Darryl Calloway
7:30 Breakfast in Williamsburg
8:30 Board bus for Yorktown
9:30 Board the North Star

Chesapeake Bay
10:30 Onboard lecture and discussion with T. Stephen Whitman, author of Challenging Slavery in the Chesapeake: Black and White Resistance to Human Bondage, 1775-1865
12:30 Box lunch aboard North Star
1:30 Onboard discussion of the Pearl incident (1848) with Jill Ogline, Associate Director of the C.V. Starr Center for the Study of the American Experience.
4:00 Arrive in St. Mary’s City, check in to rooms
5:00 Orientation and tour of St. Mary’s City
6:30 Crab feast on the bluff behind the State House
7:30 Free time
THURSDAY, JULY 12
ST. MARY’S CITY TO ALEXANDRIA
Maryland’s first capital was built upon the success of tobacco cultivation. This prosperity offered great promise to some residents and extracted a heavy price from others, particularly the bondsmen and bondswomen on whose labor the fast-growing Chesapeake economy depended. Yet the region also served as the cradle of a new and distinctively American culture, blending elements of Africa, Europe, and the New World. A day of hands-on programming will begin with an examination of artifacts unearthed by St. Mary’s City archaeologists and discussion of bringing archaeology and artifacts into the classroom. Moving north along the Patuxent River to the tidewater plantation of Sotterley, we will explore both the 1703 mansion and a rare 1830s slave house, while learning about Sotterley’s innovative approaches to teaching history by using site-specific primary sources, archaeological excavations, and the landscape. Late in the afternoon, we will leave the soil of the “Free State” and cross again into Virginia, ending the day in Alexandria – once one of the nation’s largest export markets for the sale of slaves to the Deep South, but also home to a substantial free black community in antebellum times.
Daily bloggers: Monica Jett, Amy Roos

St. Mary’s City Statehouse
7:30 Breakfast at St. Mary’s College
9:00 Joint lecture by Iris C. Ford and Henry Miller, Historic St. Mary’s City
11:00 Board bus
11:30 Arrive at Sotterley Plantation
11:45 Box lunch on the portico
Alexandria Academy Building,
Site of a school founded by
free blacks in 1812
12:30 Slavery and Freedom program with Caroline Hoey
2:00 Board bus
3:30 Arrive in Alexandria, check in at Old Town Alexandria Crown Plaza
5:30 Dinner TBA
6:30 African-American History Tour of Alexandria
7:30 Free time
FRIDAY, JULY 13
MOUNT VERNON
George Washington’s iconic place in the American pantheon and complicated relationship to slavery – controversial even in his own lifetime – make him a worthy subject as we discuss the moral, political, and psychic challenges that slavery posed for whites as well as blacks. The renowned author Henry Wiencek will set the stage with a lecture on the paradoxes, both individual and national, embodied in Washington’s relationship with slavery. Moving to his estate at Mount Vernon, our group will learn about slave life on the plantation and the relationship between the Washington family and members of its enslaved work force. We will meet staff members engaged in interpreting this history, as well as the direct descendant of Washington slaves. A lesson plan workshop will serve as capstone to the day, offering participants an opportunity to experiment with ways to bring what we have learned into the classroom.
Daily Bloggers: Jamie Hoopes, Mark Lowrie
7:30 Breakfast at Crowne Plaza Hotel
9:00 Lecture by Henry Wiencek, author of An Imperfect God, "A Paradox to Posterity": George Washington and Slavery”
Location: The Lyceum of Alexandria (c. 1839)
10:00 Board bus for Mount Vernon
10:45 Slave Life Tour with Ellen Stanton, Lead Student Programs Interpreter

George Washington’s Mount Vernon
12:00 A Conversation with Judge Rohulamin Quander, descendant of Washington slaves and Quander family historian
12:30 Lunch
1:45 Mansion Tour
2:30 Q&A with Anne Bay, Associate Director of Education, Mount Vernon
3:00 Lesson plan workshop in APC Room
5:30 Return to hotel
6:00 Dinner
7:30 Free time
SATURDAY, JULY 14
MOUNT VERNON TO WASHINGTON, DC
The final day of the journey takes the group across the Potomac into the nation’s capital, long a point of contention between efforts to defend slavery and struggles for freedom. In the streets, print shops, private homes, and government buildings of the city, proslavery, anti-slavery, and middle-of-the-road citizens alike struggled to carve their vision upon the capital. A visit to Frederick Douglass’s home at Cedar Hill, where he lived from 1877 until his death in 1895, will close the circle that we began a week ago on the banks of the Tuckahoe. Edward C. Smith of American University will help us to understand the crucial role that Douglass played during and after the Civil War. A stop at the Freedmen’s Memorial in Lincoln Park – dedicated in April 1876 with an oration by Douglass himself – will provide participants an enduring image of the task before them: teaching students to understand and challenge the legacies of slavery that still form part of our national landscape. At a final meal together, participants will share their thoughts and reflections on the journey we have just completed.
Daily bloggers: Shelly Westergard, Samantha Blau
7:30 Breakfast at Crowne Plaza Hotel
8:30 Board bus for Washington, DC

Frederick Douglass National Historic Site
9:30 Tour of Frederick Douglass National Historic Site
10:30 Meet with Edward C. Smith, Director of American Studies, American University
12:30 Final presentations and lunch at a restaurant on Capitol Hill
2:30 Board bus for Chestertown
4:00 Arrive in Chestertown
A Chesapeake Journey: From Slavery to Freedom